Reaktion #497068

Reaktionsgleichung

Na(OAc)3BH

1-Boc-azetidin-3-one

Na(OAc)3BH

1c

tert-Butyl 3-benzamidoazetidine-1-carboxylate

CF3CO2H

1-Boc-azetidin-3-one

→

compound 1e

Ausbeute 53.5%

tert-Butyl 3-benzamido-[1,3′-biazetidine]-1′-carboxylate

Ausbeute 53.5%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction was concentrated
2. 2
   workup.DISSOLUTIONthe resulting residue was dissolved in a mixed solution of 1,2-dichloroethane (10 mL) and acetic acid (0.5 mL)
3. 3
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 20 h
4. 4
   workup.STIRRINGThe reaction was stirred for another 6 h before it
5. 5
   Sonstigewas quenched by the addition of aq. NaHCO3
6. 6
   ExtraktionThe resulting mixture was extracted with CH2Cl2
7. 7
   TrocknenThe organic solution was dried over Na2SO4
8. 8
   Einengenconcentrated
9. 9
   SonstigePurification by flash column chromatography (silica gel, 4% MeOH/CH2Cl2)

Vorschrift

To a solution of 1c (1.45 g, 5.25 mmol) in CH2Cl2 (20 mL) at room temperature was added CF3CO2H (5 mL). The reaction was stirred at room temperature for 1.5 h. The reaction was concentrated and the resulting residue was dissolved in a mixed solution of 1,2-dichloroethane (10 mL) and acetic acid (0.5 mL). To the resulting solution at room temperature was added 1-Boc-azetidin-3-one 1d (0.99 g, 5.79 mmol), followed by Na(OAc)3BH (1.23 g, 5.80 mmol). The reaction mixture was stirred at room temperature for 20 h. Additional 1-Boc-azetidin-3-one 1d (0.50 g, 2.92 mmol) and Na(OAc)3BH (0.62 g, 2.92 mmol) was added. The reaction was stirred for another 6 h before it was quenched by the addition of aq. NaHCO3. The resulting mixture was extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated. Purification by flash column chromatography (silica gel, 4% MeOH/CH2Cl2) gave compound 1e (0.93 g).

Quelle